6,7,8,9-tetrahydro-5-methoxy-4-methylbenzofuro[3,2-g]coumarin | 113816-78-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,7,8,9-tetrahydro-5-methoxy-4-methylbenzofuro[3,2-g]coumarin
• 英文别名: 5-Methoxy-4-methyl-6,7,8,9-tetrahydro-[1]benzofuro[3,2-g]chromen-2-one
• CAS: 113816-78-7
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: AAELMSZLBXWARS-UHFFFAOYSA-N

物化性质

• 沸点：
  488.4±45.0 °C(predicted)
• 密度：
  1.275±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrahydro-5-methoxy-4-methylbenzofuro[3,2-g]coumarin 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 2.0h， 以98%的产率得到5-Hydroxy-4-methyl-6,7,8,9-tetrahydro-[1]benzofuro[3,2-g]chromen-2-one
  参考文献：
  名称：

  New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity

  摘要：

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.

  DOI：

  10.1021/jm9910829
• 作为产物：
  描述：

  夫拉美诺 在 sodium hydroxide 、 硫酸 、 水 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 6,7,8,9-tetrahydro-5-methoxy-4-methylbenzofuro[3,2-g]coumarin
  参考文献：
  名称：

  Antonello, Cipriano; Zagotto, Giuseppe; Miranda, Rocio, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 11, p. 651 - 654

  摘要：

  DOI：

文献信息

• Synthesis of Linear and Angular Benzofurocoumarins
  作者：Carmen Terán、Rocio Miranda、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1055/s-1997-1381

  日期：1997.12

  A four-step synthetic approach to substituted linear and angular benzofurocoumarins is described. Starting from 5-methoxyresorcinol, this approach afforded good yields of benzopsoralen (7), benzoangelicine (8), and benzoallopsoralen (11), which bear easily hydrolysed methoxy groups and thus allow access to other substituted compounds with potential as photochemotherapeutic agents.

  描述了取代的线性和有角苯并呋喃香豆素的四步合成方法。从 5-甲氧基间苯二酚开始，这种方法获得了苯并补骨脂素 (7)、苯并当归素 (8) 和苯并别补骨脂素 (11) 的良好产率，它们带有容易水解的甲氧基，因此可以得到其他有潜力作为光化疗剂的取代化合物。
• Ahluwalia, Vinod Kumar; Adhikari, Raju; Singh, Rishi Pal, Acta Chimica Hungarica, 1987, vol. 124, # 3, p. 427 - 430
  作者：Ahluwalia, Vinod Kumar、Adhikari, Raju、Singh, Rishi Pal

  DOI：——

  日期：——
• A new benzoangelicin with strong photobiological activity
  作者：Lourdes Santana、Eugenio Uriarte、Lisa Dalla Via、Ornella Gia

  DOI：10.1016/s0960-894x(99)00640-x

  日期：2000.1

  Benzoangelicins 4-6 were synthesized in good yields from 7-hydroxy-5-methoxy-4-methylcoumarin (1). In the absence of UVA radiation, compounds 5 and 6 were only weakly active against HL60 and HeLa tumour cells; in its presence, compound 6 was 10 times more active than the reference compound 8-methoxypsoralen. None of 4-6 exhibited cutaneous phototoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• AHLUWALIA, VINOD KUMAR;ADHIKARI, RAJU;SINGH, RISHI PAL, ACTA CHIM. HUNG., 124,(1987) N 3, 427-429
  作者：AHLUWALIA, VINOD KUMAR、ADHIKARI, RAJU、SINGH, RISHI PAL

  DOI：——

  日期：——
• Antonello, Cipriano; Zagotto, Giuseppe; Miranda, Rocio, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 11, p. 651 - 654
  作者：Antonello, Cipriano、Zagotto, Giuseppe、Miranda, Rocio、Uriarte, Eugenio

  DOI：——

  日期：——